In this Stork enamine reaction, cyclohexanone is reacted with pyrrolidine in the presence of p-TsOH catalysis to produce an enamine. This enamine undergoes.
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Organic Chemistry Hardcover 6th ed. The Stork enamine alkylationinvolves the addition of an enamine to an alpha, beta-unsaturated carbonyl acceptor in a process similar to the Michael reaction.
Views Read Edit View history. The end product is a 1,5 dicarbonyl compound. Enamines act as nucleophiles in a fashion similar to enolates. Formation of an enamine Step 2: Because of this enamines can be used as synthetic equivalents as enolates in many reactions.
Illustrated Glossary of Organic Chemistry – Stork enamine reaction
The imine is then reacted with an Grignard reagent to the corresponding magnesium salt to an intermediate capable of displacing a halide. Steven Farmer Sonoma State University.
Some of the advantages of using an enamine over and enolate are enamines are neutral, easier to prepare, and usually prevent the overreaction problems plagued by enolates. Hydrolysis once again yields the alkylated ketone. Enamined undergo an S N 2 reaction with reactive alkyl halides to give the iminium salt. In this method a carbonyl compound is converted to an imine by alkylimino-de-oxo-bisubstitution with a primary amine. Carbon-carbon bond forming reactions Name reactions. Retrieved from ” https: The iminium salt can be hydrolyzed back into the carbonyl.
This process requires a three steps: Use dmy dates from June From Wikipedia, the free encyclopedia. Michael Addition using Enamines Enamines, like other weak bases, add 1,4 to enones. In other projects Wikimedia Commons.
These reactions are generally known as the Stork enamine reaction after Gilbert Stork of Columbia University who originated the work.
When the electrophile is an acyl halidea 1,3- diketone is formed Stork acylation.
Enamines, like other weak bases, add 1,4 to enones.